Facile Synthesis of Novel, Structurally Diverse Azo Disperse Dyes by Employing Ugi Four-Component Reaction

doi:10.6023/cjoc202010033

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1703-1711.DOI: 10.6023/cjoc202010033 Previous Articles Next Articles

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基于Ugi四组分反应合成结构多样的新型分散染料

郭小燕^a, 方帅军^b, 钱红飞^b, 冯高峰^a^,^*()

a 绍兴文理学院浙江省精细化学品传统工艺替代技术研究重点实验室浙江绍兴 312000
b 绍兴文理学院纺织服装学院浙江绍兴 312000

收稿日期:2020-10-22 修回日期:2020-11-13 发布日期:2020-12-05
通讯作者: 冯高峰
基金资助:
国家自然科学基金(21676166)

Facile Synthesis of Novel, Structurally Diverse Azo Disperse Dyes by Employing Ugi Four-Component Reaction

Xiaoyan Guo^a, Shuaijun Fang^b, Hongfei Qian^b, Gaofeng Feng^a^,^*()

a Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang 312000
b College of Textile and Garment, Shaoxing University, Shaoxing, Zhejiang 312000

Received:2020-10-22 Revised:2020-11-13 Published:2020-12-05
Contact: Gaofeng Feng
About author:
* Corresponding author. E-mail: chfeng@usx.edu.cn
Supported by:
National Natural Science Foundation of China(21676166)

1. cjoc202010033辅助材料.pdf(3310KB)

Abstract

A novel approach has been established for synthesizing novel structurally diverse azo disperse dyes with good fastness properties by employing Ugi four-component reaction as the key step. 15 new disperse azo dyes were synthesized efficiently from readily available starting materials with simple operations through a sequence of generation of 4-(2-(ethyl (phenyl)amino)ethoxy)-4-oxobutanoic acid, the Ugi four-component reactions of the acid with anilines, benzaldehydes and cyclohexyl isocyanide, and the coupling of the Ugi adducts with aryl diazonium salts. The structures of Ugi adducts and the new dyes were fully characterized with ¹H NMR, ¹³C NMR, IR, MS, and HRMS. Visible absorption measurements and molar extinction coefficients were also carried out. It was found that the obtained dyes exhibited improved fastness properties on both polyamide (PA) and poly(ethylene terephthalate) (PET) fabrics as compared with C. I. Disperse Red 1 and C. I. Disperse Red 13. The improvement of fastness properties should be attributed to the introduced two amides and one ester functionalities, and the appropriately increased molecular weight/size. It is an attractive approach for accessing a library of novel azo disperse dyes with good fastness properties.

Key words: azo disperse dye, Ugi four-component reaction, diversity-oriented synthesis, fastness property, hydrogen-bonding interaction

Cite this article

Xiaoyan Guo, Shuaijun Fang, Hongfei Qian, Gaofeng Feng. Facile Synthesis of Novel, Structurally Diverse Azo Disperse Dyes by Employing Ugi Four-Component Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1703-1711.

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Fig. & Tab. 5

References 12

[1]	(a) Gharanjig, K.; Arami, M.; Bahrami, H.; Movassagh, B.; Mohamoodi, N.M.; Rouhani, S. Dyes Pigm. 2008, 76,684.
	Wang, J.-X.; Zhang, S.-F.; Tang, B.-T.; Yang, J.-Z.; Zhao, D. Dyest. Color. 2006, 43,5. (in Chinese)
	( 王杰雄, 张淑芬, 唐炳涛, 杨锦宗, 赵丹, 染料与染色, 2006, 43,5.)
[2]	(a) Rizk, H.F.; Ei-Borai, M.A.; Ei-hefnawy, G.B.; Ei-sayed, H.F. Chin. J. Chem. 2009, 27,1359.
	(b) Yazdanbakhsh, M.R.; Mohammadi, A.; Mohajerani, E.; Nemati, H.; Nataj, N.H.; Moheghi, A.; Naeemikhah, E. J. Mol. Liq. 2010, 151,107.
	(c) Deshmukh, M.S.; Sekar, N.A. Dyes Pigm. 2014, 103,25.
[3]	(a) Satam, M.A.; Raut, R.K.; Sekar, N. Dyes Pigm. 2013, 96,92.
	(b) Qiu, J.; Tang, B.; Ju, B.; Zhang, S.; Jin, X. Dyes Pigm. 2020, 173,107920.
[4]	(a) Ameuru, U.S.; Yakubu, M.K.; Bello, K.A.; Nkeonye, P.O.; Halimehjani, A.Z. Dyes Pigm. 2018, 157,190.
	(b) Fang, S.; Feng, G.; Guo, Y.; Chen, W.; Qian, H. Dyes Pigm. 2020, 176,108225.
	(c) Demirçalı, A.; Karcı, F.; Avinc, O.; Kahrıman, A.U.; Gedik, G.; Bakan, E. J. Mol. Struct. 2019, 1181,8.
[5]	(a) Qiu, J.; Xiao, J.; Tang, B.; Ju, B.; Zhang, S. Dyes Pigm. 2019, 160,524.
	(b) Cui, Z.; Cheng, X.; Li, X.; Lu, H.H.; Wang, X.D.; Chen, W.G. Chin. Chem. Lett. 2014, 25,1121.
[6]	(a) Nazeri, M.T.; Farhid, H.; Mohammadian, R.; Shaabani, A. J. Org. Chem. 2018, 83,12921. pmid: 33052681
	(b) Shaabani, S.; Dömling, A. Angew Chem., Int. Ed. 2018, 57,16266. pmid: 33052681
	(c) Feng, Q.Y.; Zhu, J.; Wang, M.-X.; Tong, S. Org. Lett. 2020, 22,483. pmid: 33052681
	(d) Pertejo, P.; González-Saiz, B.; Quesada, R.; García-Valverde, M. J. Org. Chem. 2020, 85,14240. pmid: 33052681
[7]	Li, X.; Jia, X.; Yin, L. Chin. J. Org. Chem. 2007, 37,2237. (in Chinese)
	( 李修明, 贾学顺, 殷亮, 有机化学, 2017, 37,2237.)
[8]	Madhavachary, R.; Zarganes-Tzitzikas, T.; Patil, P.; Kurpiewska, K.; Kalinowska-Tłuścik, J.; Dömling, A. ACS Comb. Sci. 2018, 20,192.
[9]	Hoffer, L.; Voitovich, Y.V.; Raux, B.; Carrasco, K.; Muller, C.; Fedorov, A.Y.; Derviaux, C.; Amouric, A.; Betzi, S.; Horvath, D.; Varnek, A.; Collette, Y.; Combes, S.; Roche, P.; Morelli, X. J. Med. Chem. 2018, 61,5719.
[10]	(a) Sehlinger, A.; Verbraeken, B.; Meier, M.; Hoogenboom, R.A. R. Polym. Chem. 2015, 6,3828.
	(b) Kakuchi, R. Angew. Chem., Int. Ed. 2014, 53,46.
[11]	Rocha, R.O.; Rodrigues, M.O.; Neto, B.A. D. ACS Omega 2020, 5,972.
[12]	Li, H.; Qian, H.-F.; Feng, G. Dye Pigm. 2019, 165,415.

Dye	λ_max/nm	Δν_1/2^a/nm	ε/(L?mol^–1?cm^–1)
C. I. Disperse Red 1	502	113	35995
C. I. Disperse Red 13	522	124	34118
3aa	489	112	32742
3ab	509	124	28178
3ac	436	128	24983
3ba	483	119	40043
3bb	507	132	34483
3bc	436	125	26115
3ca	486	114	27067
3cb	508	126	26042
3cc	440	124	23121
3da	487	117	36157
3db	509	134	33758
3dc	439	124	25128
3ea	490	119	40267
3eb	510	124	38953
3ec	442	128	30263

Dye	λ_max/nm	Δν_1/2^a/nm	ε/(L?mol^–1?cm^–1)
C. I. Disperse Red 1	502	113	35995
C. I. Disperse Red 13	522	124	34118
3aa	489	112	32742
3ab	509	124	28178
3ac	436	128	24983
3ba	483	119	40043
3bb	507	132	34483
3bc	436	125	26115
3ca	486	114	27067
3cb	508	126	26042
3cc	440	124	23121
3da	487	117	36157
3db	509	134	33758
3dc	439	124	25128
3ea	490	119	40267
3eb	510	124	38953
3ec	442	128	30263

Dye	Washing							Sublimation		Light	Rubbing
	Change	Staining^a						Change	Staining	Change	Dry	Wet
	Change	D	C	N	PET	PAN	W	Change	Staining	Change	Dry	Wet
C. I. Disperse Red 1	2	1	2~3	1	3	4	1~2	3~4	2	3	5	4~5
C. I. Disperse Red 13	2	1	2~3	1	3	4	2	4	2~3	2~3	5	4~5
3aa	3	5	5	4~5	5	5	5	3	5	4	4~5	4~5
3ab	4	4~5	4~5	4	4~5	5	4~5	3~4	5	3~4	4~5	4
3ac	4	4~5	4~5	4~5	4~5	5	4~5	4~5	4~5	4	4~5	4
3ba	4~5	5	4~5	4~5	5	5	4~5	4~5	4~5	4	5	5
3bb	4~5	3~4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3bc	4	4~5	4~5	4	4~5	5	4~5	4~5	4~5	4	3~4	4~5
3ca	4~5	3	4~5	3	4~5	4~5	4~5	4~5	4	4	4~5	3~4
3cb	4	3~4	4~5	3	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3cc	3~4	3~4	4~5	3~4	4~5	4~5	4~5	4~5	4~5	4	3	2~3
3da	4	4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4	4~5
3db	4~5	4~5	4	4~5	4~5	5	5	4	5	3~4	5	4
3dc	2~3	3~4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3ea	2~3	2~3	4~5	2	4~5	5	4	4	3~4	3~4	5	5
3eb	3	3	4~5	2~3	4~5	5	4~5	4	4~5	2~3	4~5	4~5
3ec	3	3	4~5	3	4~5	4-5	4~5	4	4~5	4~5	4~5	5

Dye	Washing							Sublimation		Light	Rubbing
	Change	Staining^a						Change	Staining	Change	Dry	Wet
	Change	D	C	N	PET	PAN	W	Change	Staining	Change	Dry	Wet
C. I. Disperse Red 1	2	1	2~3	1	3	4	1~2	3~4	2	3	5	4~5
C. I. Disperse Red 13	2	1	2~3	1	3	4	2	4	2~3	2~3	5	4~5
3aa	3	5	5	4~5	5	5	5	3	5	4	4~5	4~5
3ab	4	4~5	4~5	4	4~5	5	4~5	3~4	5	3~4	4~5	4
3ac	4	4~5	4~5	4~5	4~5	5	4~5	4~5	4~5	4	4~5	4
3ba	4~5	5	4~5	4~5	5	5	4~5	4~5	4~5	4	5	5
3bb	4~5	3~4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3bc	4	4~5	4~5	4	4~5	5	4~5	4~5	4~5	4	3~4	4~5
3ca	4~5	3	4~5	3	4~5	4~5	4~5	4~5	4	4	4~5	3~4
3cb	4	3~4	4~5	3	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3cc	3~4	3~4	4~5	3~4	4~5	4~5	4~5	4~5	4~5	4	3	2~3
3da	4	4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4	4~5
3db	4~5	4~5	4	4~5	4~5	5	5	4	5	3~4	5	4
3dc	2~3	3~4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3ea	2~3	2~3	4~5	2	4~5	5	4	4	3~4	3~4	5	5
3eb	3	3	4~5	2~3	4~5	5	4~5	4	4~5	2~3	4~5	4~5
3ec	3	3	4~5	3	4~5	4-5	4~5	4	4~5	4~5	4~5	5

Dye	Washing							Sublimation		Light	Rubbing
	Change	Staining^a						Change	Staining	Change	Dry	Wet
	Change	D	C	N	PET	PAN	W	Change	Staining	Change	Dry	Wet
C. I. Disperse Red 1	4~5	4~5	5	4~5	5	5	5	3~4	2	4	5	5
C. I. Disperse Red 13	4	5	5	4~5	5	5	5	4	2~3	4	4~5	5
3aa	4	5	5	5	5	5	5	4	5	4~5	4~5	5
3ab	4~5	4~5	4~5	5	5	5	5	3~4	5	6	4~5	5
3ac	5	5	5	5	5	5	5	4~5	5	7	4~5	5
3ba	5	5	4~5	5	5	5	5	4~5	5	4	5	5
3bb	5	5	4~5	5	5	5	5	5	5	6	5	5
3bc	4~5	5	5	5	5	5	5	4~5	4~5	6	5	5
3ca	4~5	5	5	5	5	5	5	4~5	4~5	4~5	4~5	5
3cb	4	5	5	4~5	5	5	5	5	4~5	6	3~4	4~5
3cc	4~5	5	5	5	5	5	5	4~5	5	7	5	5
3da	5	5	4~5	5	5	5	5	4~5	4~5	4	5	5
3db	4~5	5	5	5	5	5	5	3~4	5	4~5	3~4	4~5
3dc	5	5	5	5	5	5	5	5	4~5	6	5	5
3ea	5	4~5	5	4~5	5	5	5	4~5	4	4	4~5	5
3eb	4~5	4~5	5	4~5	5	5	5	4~5	4~5	4~5	4~5	4~5
3ec	4	4~5	4~5	4~5	5	5	5	3~4	4~5	4	4~5	5

基于Ugi四组分反应合成结构多样的新型分散染料

Facile Synthesis of Novel, Structurally Diverse Azo Disperse Dyes by Employing Ugi Four-Component Reaction

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